The Urbane Tomboys

“I dress like a boy because I feel like boys are generally more comfortable than women,” said Ali Tenenbaum the other day, sitting at a West Village coffee shop and wearing a “typical” outfit of black Hudson jeans, blue J. Crew cardigan, yellow T-shirt and designer sneakers. Ms. Tenenbaum, 38 (whose family was the inspiration for the Wes Anderson film The Royal Tenenbaums, though she said the actual resemblance is slight), has unfussy brown hair that falls to several inches above her shoulders, and clear, radiant skin. She doesn’t wear makeup. She is a professional photo organizer who meets with her (largely) Upper East Side clientele wearing sneakers. “Sometimes it throws them off a bit, but then I charm them and they’re fine with it!” she said.

It was just a few years ago that everyone was nattering about the metrosexual, the New York man who, though straight, loved his Kiehl’s and Thomas Pink tattersall shirts and is addicted to Grey’s Anatomy. Less discussed has been his female counterpart: gals who, while not lesbians, dress like guys (young guys), well into their 30’s; who leap into games of pickup basketball with male friends while the rest of us watch wanly from the sidelines; who affect a wry detachment from their sex’s conventional concerns of shoe-shopping, man-hunting and family. Think of the comedienne Sarah Silverman, mugging and shrugging and strumming her way through an “I’m F*cking Matt Damon” video, a birthday gift to her boyfriend, ABC talk-show host Jimmy Kimmel. Or matter-of-fact Juno actress Ellen Page. Or surly pop star Avril Lavigne.

And these gals are everywhere in New York. Urbane tomboys in $200 jeans, they wear sneakers to the office or the studio (they probably work in a creative industry). They’ve largely given up on mainstream women’s fashion, with its expensive, often unflattering vicissitudes, finding refuge in an eternal sporty girlhood that may or may not be tied to any real athletic bent. They borrow from men’s wear, which is more constant, comfortable and, lately, focused on well-made basics like jeans and T-shirts, and they profess ignorance of female grooming rituals, even if they have a secret love of eyeliner. Ever self-deprecating, this kind of woman is quick to tell you she “wears the same thing every day,” or that she dresses like her husband or boyfriend.

‘I Like to Keep It Basic’

In between glamorous appearances at awards shows, Ms. Silverman and Ms. Page—as well as more mainstream examples like Jessica Biel, Drew Barrymore and Cameron Diaz—seem to revel in sneakered, hoodied androgyny, thereby recasting femininity as something you can take off and put on again: an optional, mildly silly act that certainly seems to excite everyone but that one needn’t always make time for.

Ms. Silverman, particularly, whose status as a sex object is partly the product of the tension created by her potty mouth and her JAP-y good looks, dresses like she’s on her way to intramural softball. It’s a look that basically says, I’m too cool for dresses, a direct commentary on an ever-more-exhausting mainstream feminine aesthetic. The urbane tomboy cares without seeming to care. Because she’s hot enough to succeed without the embellishment, and she knows this.

Key to this type is a certain willful naïveté about the baffling stratagems of conventional female life.

“I do try to be more girly,” Ms. Tenenbaum said with a shrug. “I try to buy poufy sleeves, even just a cardigan with a poufy sleeve. And I put it on and I just can’t do it.”

They like to order Scotch at bars, rather than fruity drinks like cosmos; roll their own cigarettes; and profess to not know their way around a powder puff.

“I have my products. But I’m sure I don’t know what the hell I’m doing,” said Gillian Schwartz, 30, co-owner of a brand consulting firm, Parisi, whose high-profile fashion clients includes Vena Cava and Steven Alan. “When they start getting too specialized or tricky. … I guess I don’t like tricky. … Essentially, if you’re a pretty lady, you can just kind of let that …” She trailed off. “Well, I have no idea where I am on that, but I just like to keep it basic.”

Ms. Schwartz, a tall, bare-faced brunette, was drinking cappuccino in Nolita near her office the other day in a monochrome shirt and cardigan combo and slim brown corduroys. “I almost feel clownish when I get dressed up,” she said, echoing Ms. Tenenbaum. “There’s a real apprehension, especially in the creative industries, to not be overdressed. Overdressed is pretty bad. Underdressed is cool.”

To be an urbane tomboy is to have a certain condescension toward feminine adornment (even, or especially, when it’s the source of one’s livelihood). Or at least, a sense that in serious times, we should be thinking about other things. “Maybe people don’t feel as comfortable being all blinged out anymore,” suggested Ms. Schwartz. “There’s some bad stuff going on that we’re responsible for.”

The Urbane Tomboys